WO2017075590A2 - Procédés de préparation de 2-dihalo-ribolactones - Google Patents

Procédés de préparation de 2-dihalo-ribolactones Download PDF

Info

Publication number
WO2017075590A2
WO2017075590A2 PCT/US2016/059721 US2016059721W WO2017075590A2 WO 2017075590 A2 WO2017075590 A2 WO 2017075590A2 US 2016059721 W US2016059721 W US 2016059721W WO 2017075590 A2 WO2017075590 A2 WO 2017075590A2
Authority
WO
WIPO (PCT)
Prior art keywords
group
alkyl
formula
compound
cycloalkyl
Prior art date
Application number
PCT/US2016/059721
Other languages
English (en)
Other versions
WO2017075590A3 (fr
Inventor
Ozkan SARI
Coralie DE SCHUTTER
Jong-Hyun Cho
Longhu Zhou
Hongwang ZANG
Franck Amblard
Steven J. Coats
Raymond F. Schinazi
Original Assignee
Cocrystal Pharma, Inc.
Emory University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cocrystal Pharma, Inc., Emory University filed Critical Cocrystal Pharma, Inc.
Priority to US15/772,294 priority Critical patent/US20190077797A1/en
Publication of WO2017075590A2 publication Critical patent/WO2017075590A2/fr
Publication of WO2017075590A3 publication Critical patent/WO2017075590A3/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/6574—Esters of oxyacids of phosphorus
    • C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
    • A61K31/708—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid having oxo groups directly attached to the purine ring system, e.g. guanosine, guanylic acid

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

La présente invention concerne des procédés de formation d'intermédiaires de 2-bromo,2-fluororibofuranose et d'intermédiaires de 2-chloro,2-fluororibofuranose destinés à être utilisés dans la préparation de nucléosides antiviraux. L'invention porte également sur des procédés de fabrication de nucléosides et des promédicaments nucléosidiques, au moyen des intermédiaires. Ces procédés produisent tous des intermédiaires et leurs nucléosides et promédicaments en résultant, la chiralité du carbone à la position 2 étant régulée. Dans certains modes de réalisation, la chimie implique l'utilisation d'auxiliaires chiraux, tels que (R)-2,2-diméthyl-l,3-dioxolane-4-carbaldéhyde, et dans d'autres modes de réalisation, la chimie implique l'utilisation de matériaux de départ chiraux, tels que le D-xylose.
PCT/US2016/059721 2015-10-30 2016-10-31 Procédés de préparation de 2-dihalo-ribolactones WO2017075590A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US15/772,294 US20190077797A1 (en) 2015-10-30 2016-10-31 Processes for preparing 2-dihalo ribolactones

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201562248652P 2015-10-30 2015-10-30
US62/248,652 2015-10-30

Publications (2)

Publication Number Publication Date
WO2017075590A2 true WO2017075590A2 (fr) 2017-05-04
WO2017075590A3 WO2017075590A3 (fr) 2017-07-20

Family

ID=58630829

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2016/059721 WO2017075590A2 (fr) 2015-10-30 2016-10-31 Procédés de préparation de 2-dihalo-ribolactones

Country Status (2)

Country Link
US (1) US20190077797A1 (fr)
WO (1) WO2017075590A2 (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI678369B (zh) * 2014-07-28 2019-12-01 美商基利科學股份有限公司 用於治療呼吸道合胞病毒感染之噻吩並［３,２-ｄ］嘧啶、呋喃並［３,２-ｄ］嘧啶及吡咯並［３,２-ｄ］嘧啶化合物類

Also Published As

Publication number Publication date
US20190077797A1 (en) 2019-03-14
WO2017075590A3 (fr) 2017-07-20

Similar Documents

Publication Publication Date Title
US11718638B2 (en) Compounds, compositions and methods for synthesis
KR101759369B1 (ko) 인을 함유하는 활성물의 입체선택성 합성
RU2720811C2 (ru) 4'-замещенные нуклеозидные ингибиторы обратной транскриптазы и их получение
EP0342203B1 (fr) Derives d'oxyde de 2',3' didesoxyribofuranne
JP6663424B2 (ja) 癌の処置のためのウリジンのジオキソラン類似体
MXPA04005779A (es) Nucleosidos de n4-acilcitosina para el tratamiento de infecciones virales.
AU2002365234A1 (en) N4-acylcytosine nucleosides for treatment of viral infections
AU2002255654A1 (en) Method for the synthesis of 2',3'-dideoxy -2',3'-didehydronucleosides
WO2002070533A2 (fr) Procede de synthese de 2',3'-dideoxy-2',3'-didehydronucleosides
EP1745573A2 (fr) Procedes de fabrication de 2'-desoxy-&g(b)-l-nucleosides
WO1991019713A1 (fr) Derive de nucleoside de pyrimidine
CN113164506A (zh) 二核苷酸化合物及其前体药物
KR102351734B1 (ko) 2'-플루오로-6'-메틸렌-탄소환식 아데노신(fmca) 및 2'-플루오로-6'-메틸렌-탄소환식 구아노신(fmcg)의 합성
US5432273A (en) Preparation of 3'-substituted-2',3'-dideoxynucleosides and 2'-deoxynucleosides from acyclic, achiral precursors
Yoshimura et al. Synthesis of 1-(5, 6-dihydro-2H-thiopyran-2-yl) uracil by a Pummerer-type thioglycosylation reaction: the regioselectivity of allylic substitution
WO2017075590A2 (fr) Procédés de préparation de 2-dihalo-ribolactones
CN111051325A (zh) 螺硫杂环丁烷核苷
AU2009313842B2 (en) Method of preparing deoxyribofuranose compounds
KR101259648B1 (ko) 2′,2′-디플루오로뉴클레오시드 및 중간체의 새로운 제조방법
Schmidt et al. A Direct Synthesis of Nucleoside Analogs Homologated at the 3′‐and 5′‐Positions
Ichikawa et al. Synthesis of 3′-β-carbamoylmethylcytidine (CAMC) and its derivatives as potential antitumor agents
Swamy et al. Synthesis of N-homobicyclic dideoxynucleoside analogues
Pei et al. Synthesis of 3′-C-hydroxymethyl-substituted pyrimidine and purine nucleosides as potential anti-hepatitis C virus (HCV) agents
WO2022256490A2 (fr) Synthèse améliorée de phosphoramidates pour le traitement du virus de l'hépatite b
JP2014169239A (ja) 核酸誘導体とその製造方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16861042

Country of ref document: EP

Kind code of ref document: A2

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16861042

Country of ref document: EP

Kind code of ref document: A2